In Part 2, Waverly Deutsch opens up about her decades at Chicago Booth, where she helped founders refine not just their business models but their ability to lead. She discusses how emotional connection strengthens logic, why confident delivery isn’t enough, and how AI is changing but not replacing human insight. For Gen Xers mentoring across generations or rethinking their own leadership, this episode is a reminder: great guidance begins with deep listening.Coaching Across the Confidence Spectrum“Some people came in over-confident. Some barely made eye contact.”She explains how coaching required tailoring—not templating—entrepreneurs’ thinking.Why Love Belongs in Leadership“If you can’t connect with your idea, why should anyone else?”Waverly talks about the human element most founders overlook when presenting.Building Trust Across Generations“EMBAs bring wisdom. Undergrads bring fire.”She shares the challenge—and joy—of coaching both seasoned execs and young dreamers.Relearning Her Own Leadership“Coaching taught me how much I still had to unlearn.”She reflects on what working with thousands of students revealed about her own blind spots.AI Is Here—Now What?“AI can write your pitch. But can it build your conviction?”She discusses how tech is changing communication—and why human trust still drives every great pitch._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Waverly Deutsch and what is her coaching philosophy?
Chapter 2: What challenges do logical entrepreneurs face at Chicago Booth?
where you've dedicated 22 years to teaching and coaching the environment there was highly structured and students ranging from college undergrads to full-time mbas about mid-20s and late 20s and executives who are mid-30s to mid-40s All of them represented a distinctly logical and talented group of people.
Many of these students, like myself, came from very strong corporate backgrounds where we were primarily trained to think with our heads over our head. With that in mind, I'm curious about your perspective about them. They came to you. very eager to explore and explode their passions for innovation, for change, and for entrepreneurship. What common challenges did you observe them facing?
That's the first part of my question. For the second part, given those challenges you've identified, how have you leveraged your own experiences to guide them? Do you find yourself offering more love, i.e. emotional support, over logic, i.e. calculated strategies? Or is it a mix of both? or depending on individuals or segments of individuals?
That's a great question. I think that the cohorts and the individuals all face some similarity of challenge and some difference of challenge. So I'll give you an example. The undergraduate population is hugely innovative because they haven't gone out into the work world yet to see the obstacles that are put in the path of creativity. Right. So we all think about innovation in a large corporation.
Have you done your homework? What's the market analysis? Do we have the resources for this? And, oh, by the way, we have to get approval from 17 layers of corporate to even have a conversation about this or create a working group about this. And eventually, the person with the idea is, never mind. There's a lot of process that's layered on top of things in the corporate world that...
sets up obstacles to innovation. I think that every corporation is aware of and battles as they want to become more innovative, but also that people become aware of as they progress in the work world. So that being said, the undergraduates don't know what's possible. They don't know what's impossible. They don't have the foundation for a lot of that logic.
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Chapter 3: How does coaching differ between undergraduate and executive MBA students?
And so the challenge with them is to give them a process and I believe entrepreneurship is a process. It's a process of taking an idea or identifying an opportunity and turning it into an organization, a company, a not-for-profit that brings a specific type of value to a specific community. in a sustainable way, right?
So either profitability or fundability in the nonprofit world, it's a process, right? It's a process of evaluating opportunities. It's a process of testing solutions. It's a process. So with undergrads, what you're really doing is you're giving them the process by which they can learn to add the logic, the data, the research to their passions.
It's almost exactly the opposite with, say, the executive MBAs. The ideas often... Lack innovation and lack creativity are incremental to the way things are being done because they are so aware of the barriers to innovation, the challenges of getting new things through. But then you say, why does the world need a company?
a tiny bit incrementally better than the way you've seen things done in the past, right? So it's really hard to break through brand loyalty, comfort without having something that's really innovative, right? How do you overcome the liability of newness? So you're right that a balance
that you have to use between managing a person's tendency to go with their heart versus their tendency to go with their head to help them bring those two things together in the set of complimentary qualities that an entrepreneur has to have. which is both the vision and the execution, right?
You have to see the potential for the future, but also be able to figure out the tiny step-by-step that's going to allow you to build the foundation of a company that can reach that vision. It is different across different cohorts, different people, whether they're in school or they're entrepreneurs in the world, but certainly at Booth,
dealing with a range of students from, I taught high school students through boots for a while, all the way to very senior, seasoned executives, it is your job as a teacher, as a coach, as a mentor, to figure out where the strengths and weaknesses are and bring techniques, tools, and advice that balances the strengths and weaknesses for that particular individual.
Can you share with us some specific examples?
Let me start with some examples from the executive level MBA program. Very often, because they've been in the corporate world, they don't want to present anything that isn't absolutely doable, low risk. And so they say, if you give us $5 million to build out this software, we can generate $7 million in five years.
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Chapter 4: What are examples of balancing love and logic in entrepreneurship coaching?
If you, the entrepreneur, don't believe that you can be a $50 million company, if you, the entrepreneur, don't believe that this is a powerful, disruptive, high-value add to your customers in such a way that if you're given this kind of capital, $5 million plus, that you can't bring it to market in a way that in five years gets you to $50 million, what's the investor going to think about the business?
Yep. Right? Yep. Then you have at the other end of the spectrum... The young entrepreneurs who are so excited about their product and they've showed it to their friends and their friends are so excited about their product. And they're like, if you give me $200,000 to put this product into the market, I will be a billion dollar company in five years. This is going to go viral.
Everybody's going to want it. It's going to just catch fire. And you say, okay, how does that happen? Can you show me an example where for so little money, somebody has been able to get so big, so fast because the product was so exciting and they'll say Groupon got to a billion dollars in a year. And I said, yeah, Groupon had tens of millions of dollars of venture backing.
They got there that fast by acquiring a lot of companies that took a lot of money. So what makes you think for a very small amount of money, you're going to be able to do it? That's a case where you're bringing the logic into it. In the case of, we are only going to get to $7 million, you've got to bring the emotion into it, the excitement, the thrill, the FOMO, as it's called in Silicon Valley.
Fear of missing out. With the... A younger entrepreneur, you've got to bring the logic back into it. What's the step-by-step? Has anybody else done it? Is there a path that you can follow, a playbook you can follow? You're definitely bringing different things in. With the full-time and part-time MBAs, it can be a little bit of both.
I'll give you an example that I've used many times, and Caitlin, forgive me if I'm getting this wrong, but I'm going to talk to you about the conversation that I had with the founder of Simple Mills, Caitlin Smith. Thank you. Caitlin came to Booth because she was working on a startup. She was working on making gluten-free baking mixes for people who suffer with celiac and gluten issues.
And she had created... using nut flour instead of many of the other gluten substitutes. A really fabulous muffin mix. I mean, it was delicious, and I hate gluten-free baked goods, but I really liked her muffins. She came and pitched in the New Venture Challenge class, and she said, here's what I've done. Here's how I did it. I'm in about... 13 health food stores in North Carolina.
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Chapter 5: How did Simple Mills evolve from a startup idea to a billion-dollar company?
Chapter 6: What role does emotional connection play in delivering a compelling business pitch?
I've got another 14 signed up, so we'll be in 27 healthcare stores and healthy stores in North Carolina area. Thank you very much." And everybody paused and said, What do you want from us? I'm not sure I want anything from you. I'm not sure I want to raise money for this. I'm not sure that I need anything from you. So the judges for the New Venture Challenge are angel investors, venture investors.
They're thinking, okay, good luck to you with your nice little lifestyle business, but there's not much we can help you with. So Caitlin and her New Venture Challenge team and I were sitting in a conference room and I was saying to her, Caitlin, I understand that you haven't thought about taking on money and scaling this business and that you're not even sure that's what you would want to do.
But you'll get the most out of this learning process and you'll get the most out of the resources of the coaches and mentors and judges that we put in front of you. If just for the sake of this exercise, you imagine...
possibilities you think big what what could this look like if you did want to take on venture capital money if it was available to you what's the upside what's the biggest you can imagine because to me this shouldn't be just in health food stores or on gluten-free shelves this is a very delicious, healthy breakfast option for anybody who wants higher protein, higher fiber, good for you muffins.
So to me, this should be on every grocery store shelf, what's the biggest independent baking goods company you can think of in the 20th century? And she immediately said, Betty Crocker. And I said to her, why shouldn't Simple Mills be the Betty Crocker of the 21st century? What if just for the sake of the new venture challenge, you modeled that out? What would that look like?
What capital would it require? What distribution channels would you use? And I could see her getting defensive. I could see her getting a little angry. I don't know if that's what I want to do. Why are you making me think about... I could imagine the things that are going on behind her eyes. Her team is literally like chewing their fingernails.
They've tried to have this conversation with her, I can tell, and they're really nervous about her reaction. She comes back later and she says, you know what, I'm going to try that. Let's maybe think about raising a couple hundred thousand dollars.
And for her second pitch in the class for the New Venture Challenge, she starts to talk about distribution at Whole Foods and she starts to have conversations with people at Whole Foods and she starts to think about the fact that gluten-free is coming on other
grocery store shelves and maybe there is bigger distribution and maybe with a few hundred thousand dollars she can expand the number of SKUs or number of products she's offering so she pitches that at the second round and she gets selected to go into the finals and by the finals she's really thinking about a seed round of six hundred thousand dollars guess what Temple Mills is a
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Chapter 7: What is the New Venture Challenge and why is it important for startups?
Chapter 8: How is AI changing coaching and leadership in entrepreneurship?
As we enter the age of AI, Waverly and I will also discuss the role of human coaches. In this still developing scenario, AI is the powerhouse of logic. While decent coaches like Waverly represent love, providing that essential human touch in the coaching process. Without further ado, let's get started. Now, let's dive into a significant chapter of your career at Chicago Booth.
where you've dedicated 22 years to teaching and coaching the environment there was highly structured and students ranging from college undergrads to full-time mbas about mid-20s and late 20s and executives who are mid-30s to mid-40s All of them represented a distinctly logical and talented group of people.
Many of these students, like myself, came from very strong corporate backgrounds where we were primarily trained to think with our heads over our head. With that in mind, I'm curious about your perspective about them. They came to you. very eager to explore and explode their passions for innovation, for change, and for entrepreneurship. What common challenges did you observe them facing?
That's the first part of my question. For the second part, given those challenges you've identified, how have you leveraged your own experiences to guide them? Do you find yourself offering more love, i.e. emotional support, over logic, i.e. calculated strategies? Or is it a mix of both? or depending on individuals or segments of individuals?
That's a great question. I think that the cohorts and the individuals all face some similarity of challenge and some difference of challenge. So I'll give you an example. The undergraduate population is hugely innovative because they haven't gone out into the work world yet to see the obstacles that are put in the path of creativity. Right. So we all think about innovation in a large corporation.
Have you done your homework? What's the market analysis? Do we have the resources for this? And, oh, by the way, we have to get approval from 17 layers of corporate to even have a conversation about this or create a working group about this. And eventually, the person with the idea is, never mind. There's a lot of process that's layered on top of things in the corporate world that...
sets up obstacles to innovation. I think that every corporation is aware of and battles as they want to become more innovative, but also that people become aware of as they progress in the work world. So that being said, the undergraduates don't know what's possible. They don't know what's impossible. They don't have the foundation for a lot of that logic.
And so the challenge with them is to give them a process and I believe entrepreneurship is a process. It's a process of taking an idea or identifying an opportunity and turning it into an organization, a company, a not-for-profit that brings a specific type of value to a specific community. in a sustainable way, right?
So either profitability or fundability in the nonprofit world, it's a process, right? It's a process of evaluating opportunities. It's a process of testing solutions. It's a process. So with undergrads, what you're really doing is you're giving them the process by which they can learn to add the logic, the data, the research to their passions.
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